Triethylamine → 5-Butylpyridine-2-carbonitrile

HRID 1650336

Reaktionsgleichung

Reaktionsgleichung von HRID 1650336
CN(C)[CH:3]=[CH:4][C:5]([NH:7][CH2:8][CH2:9][CH3:10])=[CH2:6].Cl[C:13](=[CH2:16])[C:14]#N.C([N:19](CC)CC)C>C(#N)C>[CH2:10]([C:9]1[CH:3]=[CH:4][C:5]([C:6]#[N:19])=[N:7][CH:8]=1)[CH2:14][CH2:13][CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 701982-ChloroacrylonitrileHCID 86743901HCID 86743901, Verbindung

Produkt 1

HCID 3293775-Butylpyridine-2-carbonitrileAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

0.1 mole of 1-dimethylamino-1-aza-3-n-butyl-1,3-butadiene, 0.1 mole of 2-chloroacrylonitrile and 0.2 mole of triethylamine are heated in 100 ml of acetonitrile for 20 hours to 60° C. The reaction mixture is concentrated by evaporation and the residue is dissolved in dioxane. The solution is filtered and gaseous HCl is introduced. The batch is stirred for 15 minutes at room temperature and then concentrated by evaporation. The residue is partitioned between CH2Cl2 and 1N NaHCO3. The organic phase is dried, concentrated by evaporation and distilled under a high vacuum, affording 10.0 g (63%) of a yellowish oil with a boiling point of 86°-87° C./3·10-1 mbar.

Aufarbeitung

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. dissolutionthe residue is dissolved in dioxane
  3. filtrationThe solution is filtered
  4. additiongaseous HCl is introduced
  5. concentrationconcentrated by evaporation
  6. customThe residue is partitioned between CH2Cl2 and 1N NaHCO3
  7. customThe organic phase is dried
  8. concentrationconcentrated by evaporation
  9. distillationdistilled under a high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7db52327ff8b4b44938e3cd1c4358bb6
Quelldatensatz
uspto-grants-1990_05
Patentnummer
US04923993

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